Buying a home that's not big enough - future additions?

We are in the process of looking for a home to buy. Not surprisingly, it's turning out that homes in our price range and desired locations tend to be <1000sq ft 2 bedroom homes.  Ideally we'd like more space and a 3rd bedroom as we plan to add a 2nd child in the future and have out of town family we'd like to comfortably house.  One thought is that we buy a smaller 2 bedroom home we can afford and in a couple years plan to add on a couple hundred square feet and a 3rd bedroom.  My question is how do we determine if the 2bdrm homes we're looking at would be a good fit for this? How do we determine if an attic could be converted in the future?  Or  make a subbasement useable? Do we take lot size into consideration?  What other considerations are there?

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Lot size is definitely a consideration, as it is much cheaper to add a first floor addition.  The flatness of the lot is also important.  There are regulations in most cities about what is allowable.  You will want a contractor to look at the house before you buy it to determine the feasibility of an addition.  2nd story additions sometimes require the foundation to be shored up as well.  

Your questions and concerns are understandable, but won't be easily addressed here. Contractors and architects can offer input on what's possible with any given home, but each home carries it's own variables - setbacks, foundation depth, neighbor trouble, zoning, etc. Expanding a home is a great idea conceptually, but in my experience, it rarely happens - with the average length of ownership at around 10 years, you're likely to move making the undertaking a questionable effort.  As a realtor, I suggest two ideas: 1) find a 2 bedroom home that's at least 1200 square feet in bad shape and reconfigure it or 2) broaden your location.